Synthesis and Properties of New Organosoluble Alkoxylated Naphthalene-Based Novolacs Preparaed by Addition-Condensation of Mono- or Di-alkoxynaphthalene with Formaldehyde

The preparation of new alkoxylated naphthalene-based novolacs [poly(naphthylenemethylene)s] by acid-catalyzed addition-condensation of mono- or di-methoxynaphthalene with formaldehyde is described in this paper. The polymerization of 2-methoxynaphthelene ( 1 ) with an equimolar amount of formaldehyde proceeded homogeneously to give the polymer 2 ( M n 3100, M w / M n 1.7) in good yield. The FT-IR, 1 H NMR and 13 C NMR spectra suggest that 2 might have a naphthylene-methylene unit and approximately linear polymer backbones. In contrast, in the case of 1,5-dimethoxynaphthalene ( 3a ) as a monomer, the obtained polymer ( 4a ) ( M n 1900, M w / M n 2.3) was a branched polymer. From TGA, T 10 (temperature at 10% loss in weight) indexes of the polymers 2 and 4a were estimated to be 402 and 359 °C, respectively. These results indicate that the alkoxylated naphthalene-based novolacs have good thermal stability.